Stop over organizing your Mac, let private AI find it

You promise yourself that one day you will fix your folders.

You will clean Downloads, rename everything, build the perfect hierarchy for projects, clients, invoices, screenshots, and notes. Then real work happens, more files arrive, and the tidy system never ships.

On a modern Mac with a big SSD, manual organization does not scale. You do not remember filenames, you remember moments. The slide with churn. The screenshot of the dashboard. The contract with a 60 day notice period.

With Fenn, you can stop chasing the perfect folder tree. You keep a simple structure, let private AI search index your real work on your Mac, then ask in natural language when you need to find something.

Download Fenn for Mac. Private on device. Find the moment, not the file.

Why over organizing your Mac stops working

On a small disk you can survive with:

• A few carefully maintained folders

• Strict naming rules

• Regular cleanup sessions

On a 1 or 2 TB Mac, that breaks quickly.

Daily reality looks more like this:

• New projects appear faster than you can create structures

• Files arrive from other people with random names

• Downloads and Desktop become holding areas

• Screenshots pile up and still contain important information

• Email threads, PDFs, docs, and call recordings all mix together

You end up with two bad options.

• Spend time hand curating, renaming, and reshuffling

• Give up and hope Spotlight or Finder search will be enough

Neither uses the machine you bought in a way that actually helps you think or ship.

What “private AI search” means on a Mac

Private AI search is simple.

• Your files stay on your Mac

• Your machine reads and indexes them locally

• You get a search box that understands meaning, not just filenames

• You can ask questions in natural language and combine that with exact filters

Fenn is built around that idea:

• Indexes PDFs, Office style documents, long reports

• Reads text inside images and screenshots

• Searches Apple Mail messages stored on your Mac

• Works with notes, internal docs, audio, and video, including useful timestamps

• Runs on device by default, your material stays on your Mac

You do not need to move to a new cloud. You turn the Mac you already own into a private search layer over your work.

Fenn instead of folder guilt

Fenn does not replace every bit of structure. You still want sensible top level areas. It just removes the need for perfect control.

A simple “good enough” structure

Keep it light:

• /Clients or /Projects for active work

• /Legal for contracts and NDAs

• /Finance for statements and invoices

• /Research for reports and papers

• /Screenshots or whatever you already use

• Archives that really need to stay local

Inside those folders, let reality happen. Files arrive with whatever names they have. Screenshots stack up. Exports sit next to briefs and feedback.

Then let Fenn do the hard part.

How you search instead of organize

Examples you can run once Fenn has indexed your key folders:

• “Signed MSA with Acme that mentions auto renew and 60 days notice.”

• “Board slide where churn spiked after the January price change.”

• “PDF pages and screenshots that show Stripe revenue by month in 2024.”

• “Apple Mail thread where Alice approved the new pricing last October.”

You are no longer saying “this file lives in /Clients/Acme/2024/Q1/Decks”. You are saying “I want the moment where we agreed this thing” and letting your Mac surface candidates.

You still decide which file to open. Fenn shows results with context so you can check quickly.

Search modes instead of nested folders

A lot of complex folder systems exist because people are trying to compensate for missing search modes.

Fenn gives you four.

• Semantic mode
  Ask in natural language when you remember the idea, not the exact words.
  Example, “contract pages that limit liability to yearly fees.”

• Keyword mode
  Match exact phrases when wording matters.
  Example, “termination without cause within thirty 30 days.”

• Hybrid mode
  Combine both, such as “board deck” plus a specific metric or phrase.

• Exact mode
  Force strict literal matches for IDs, invoice numbers, or error codes.

On a high end Mac, you can switch modes freely and still keep other heavy apps open. Instead of nesting folders for every variation of client, year, and topic, you let Fenn filter the mess by meaning.

Agent Mode for work that used to need a spreadsheet

Folder hierarchies break completely when the question is bigger than one file.

Examples:

• “Which NDAs auto renew and require more than 60 days notice.”

• “Invoices from vendor X above 500 dollars in 2024, grouped by month.”

• “Slides and emails where we discussed moving production to Tahoe 26.2.”

• “Screenshots and PDFs that show churn above 8 percent.”

Simple folder systems cannot do that. Manual work looks like lists, spreadsheets, and opening one document after another.

Agent Mode changes that.

• You ask a broader question

• Fenn uses models on your Mac to read across your indexed content

• You get structured answers and links back to the sources

Agent Mode works best on Macs with more memory, especially if you have a large library indexed. It also runs on 16 GB. If you want help tuning Fenn for your specific setup, you can reach out to the team.

You keep your high level folders. Agent Mode replaces the need to build a custom folder and spreadsheet for every new question.

Who can finally stop over organizing

Founders and operators

• Decks, contracts, investor updates, dashboards, screenshots.

• Fenn gives you answers like “what did we promise here” without living in Finder.

Lawyers and legal teams

• Matter folders, scans, long PDFs, Mail threads.

• Use Semantic, Keyword, and Exact modes across your cases instead of endless subfolders.

Finance and ops

• Statements, invoices, exports, and reporting PDFs.

• Use Agent Mode to answer questions about vendors, amounts, and periods.

Creators and product teams

• Raws, exports, briefs, specs, research.

• Let folders reflect projects loosely, then use Fenn to connect assets with text and decisions.

The more you tried to keep everything perfectly sorted, the more Fenn helps. Your existing mess is the input. You just stop treating manual sorting as the main job.

How to switch from sorting to searching in one afternoon

You do not have to rebuild your Mac. Start small.

1. Install Fenn on an Apple silicon Mac
   Sonoma 14 or later is recommended.

2. Pick 3 to 5 core folders
   Examples: Projects, Legal, Finance, Research, Screenshots, and your Mail storage.

3. Add them as sources in Fenn
   You stay in control. Fenn only indexes what you point it at.

4. Let Fenn index on device
   The first pass will take time if you have a lot of files. It all happens on your Mac.

5. Use Semantic mode as your default
   Ask for what you remember. Use Keyword, Hybrid, or Exact when you need strict control.

6. Try one Agent Mode question for each area
   One for contracts, one for invoices, one for board material, one for research.

After that, every new file you add to those folders is another piece of your private knowledge base. No elaborate folder rules required.

Pricing

If you have a Mac full of work, Fenn is a small addition compared to what you paid for storage and time.

• Local, 9 USD per month, billed annually
  On device indexing. Semantic and keyword search. 1 Mac. Updates. Founder support.

• Lifetime, 199 USD one time
  On device indexing. Semantic and keyword search. 1 year of updates. 1 Mac. Founder support.

You can keep feeling guilty about the state of your folders, or you can install Fenn and let private AI search use the Mac you already own.

Download Fenn for Mac. Private on device. Find the moment, not the file.

See also

• Turn your 2 TB Mac SSD into a searchable knowledge base
  /blog/2tb-mac-ssd-searchable-knowledge-base

• Which Mac to buy for private AI in 2025
  /blog/which-mac-to-buy-private-ai-2025

• The first 5 things to do on a new high end MacBook Pro
  /blog/first-things-new-high-end-macbook-pro

• Turn your Mac into a private AI agent
  /blog/private-ai-agent-mac-no-setup

• Search your screenshots on Mac, recover decisions you forgot
  /blog/search-screenshots-mac-recover-decisions